Potassium Cyanide → HCID 15406514, compound

HRID 1819785Notes

Reaction equation

HRID 1819785 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH2:11]O)[CH:2]=1.S(Cl)(Cl)=O.[C-:17]#[N:18].[K+].C([O-])(O)=O.[Na+]>C1C=CC=CC=1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH2:11][C:17]#[N:18])[CH:2]=1

Participants

6

Reactant 4

HCID 9032Potassium CyanideHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 12662983(Quinolin-3-yl)methanol

Product 1

HCID 15406514HCID 15406514, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of quinolin-3-yl-methanol (227, 3.1 g, 19.5 mmol) and thionyl chloride (Aldrich, 16.5 mL, 195 mmol) in 50 mL of benzene was refluxed for 3 h. After cooled to room temperature, the solvent was removed under reduced pressure to dryness. This crude product was used directly in the next reaction. 1H NMR (400 MHz, DMSO-d6) δ 9.20 (s, 1H), 8.82 (s, 1H), 8.21 (d, J=7.9 Hz, 1H), 8.19 (d, J=8.1 Hz, 1H), 7.97 (t, J=7.4 Hz, 1H), 7.81 (t, J=7.5 Hz, 1H), 5.09 (s, 2H). MS (EI): m/z 178 (M+H). Quinolin-3-yl-acetonitrile was synthesized from the above crude product, KCN, NaHCO3 and KI in similar manner as described in Example 221. 1H NMR (400 MHz, DMSO-d6) δ 8.87 (d, J=2.0 Hz, 1H), 8.36 (s, 1H), 8.05 (d, J=8.3 Hz, 1H), 8.03 (d, J=7.8 Hz, 1H), 7.79 (t, J=7.3 Hz, 1H), 7.65 (t, J=7.8 Hz, 1H), 4.31 (s, 2H). MS (EI): m/z 169 (M+H).

Workup

  1. customthe solvent was removed under reduced pressure to dryness
  2. customThis crude product was used directly in the next reaction

Sources & evidence

ORD record
ord-4615d0e54c464fe59cfc7d9855f9f7b0
Source dataset
uspto-grants-2009_10
Patent number
US07601841B2

Reaction notes

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